Ending the Shirtsleeves Proverb

John Knowlton, February 18, 2026 This piece was originally published in Trusts & Estates on February 18, 2026. Read the original article here The first generation makes it, the second generation spends it and the third generation loses it. You’ve probably heard some version of the “Shirtsleeves” proverb. Shirtsleeves to Shirtsleeves in three generations is […]
Having the Hard Money Talk: Family Wealth & Inheritance Strategies

In this episode, Georg Klausner sits down with John Knowlton to talk about something many families avoid-money. They discuss how open communication can strengthen relationships, why fairness in wealth isn’t always simple, and how shared decision-making can help families plan for lasting prosperity.
From Success to Significance

In this episode of the REL Freedom Podcast, Mike Swenson sits down with John to explore the importance of long-term, strategic thinking. Drawing on insights from his book Thinking for Success, John shares his perspective on building wealth, involving family, and creating meaningful mission, vision, and values statements. They discuss how money isn’t the finish […]
8,000 Feet, One Step at a Time

In this video John and Julie share a moment from their trip to Colorado, where they completed an 8,000 foot hike together, just 13 weeks after Julie’s knee surgery. With another surgery scheduled for this Friday and their parenting sabbatical out west coming in August, they reflect on resilience, family and moving forward one step […]
Abundance Through Thought

In this episode of the podcast Beyond the Velvet Rope, John reflects on how intentional thinking has shaped both personal outcomes and long-term prosperity. He shares insights from his journey in wealth management, highlighting the role of faith, shared governance and open communication in building trust across generations. The conversation emphasizes personal responsibility, early financial […]
What Happens When You Set Big Goals, But Don’t Change Anything

In this episode of UH-OH Conversations with Cohesive Leaders, Dr. Troy Hall and Ben-Jamin Toy chat with John Knowlton. John shares about how an unexpected “uh-oh” moment became a turning point for his leadership journey. He shares how embracing challenges can transform thinking, improve problem solving, strengthen strategy and planning and create opportunities for growth. […]